Red-halogen vat-dye and process of making same.



' LAN D.

'lSVFL, SWITZERLAND, ASSIGNOR TO THE FIRM F lfifi'llirAL INDUSTRY IN ensign, ()F' BASEL, SWlTZER- RED-HALOGEN VAT-DYE AND PROCESS O F MAKING SAME.

Specification of Letters Potent,

Patented March 26, 1907..

Application filed January 9,1907- Serinl No 351.4%43.

Be it known that l, (lyoiuxr linen, cheninnd (.loflli)! of philosophy, citizen of the s Repi ic, und iircsidcntoi' Basel, Switond, hm" 'nted new and useful hzilo-i S5 for the in.-inul'iurturc of the some, of which he foliou'nn: s :1. lull, clear, and exact ilescri pi ion.

Line-c. Li'ziics lir- 163th), .ilcd key 1 iunnu'l'oetu e ;y condensing sali- Since I have re d y:

. eylthioncetic in; with 153.

round het this dycstull' can be transformed IDiC QlCW exceedingly vulughle products by;

tin.

stances able to deliver 11 p halogens, as chlorin, I

suiiu \-l bromin, antimony peutschlorid, chlorid, in the presence of indill'crcutsolvents or dilucnts nitrol enzcne,glncial acetic acid, Alfie.

The invention is illustrated bythe followexamples: Example i: Twenty p: "is, by weight, of I condenserion prrniuct of su-licyltliioeeetic in. ii and isetin are finely crushed or ground and suspended in four hundred parts of nitrcbenzcne. To this suspension thirty-live in ,i'orty ports of bromin are added, and {he mixture is h ated, in the course of about one hour. in s.

ol ydrobroinic acid escape. The mass is further maintained in ebullition for about one and one-hell hoursviz., until the cssolut'sn of the dycstufl this latter is precipi snared red rut-dyeing dyestuii's :indn proc reflux apparatus g'rndnilly to ngcnrle cbulhtion, whereby great quantities fated in form. of scarlet-red flocks. By heating the dyestull with fuming; sulfuric acid a red-violet solution isohluincd, which becomes quickly luown-rcd and gives, on addition of Walter, :1 clear hright lu'own-rcd solution conlniuiug' probably a dissolved sullonic acid of the new dycslull', the said latter solution dyeing wool bright red tints. in hot alcohol and hot. benzene the brominulcd dycstull' is vcrydillicultly soluble with u rose coloration, but easily in hot nitrobcuzene with a doe rcd colorulion. (in cooling the dyestu separates in form of brilliant yellow-red felted needles. When made into a. vat with the usual reducing agents, the dyestufl' yields a bright yellow \nt. When applied by the dyeing and printing processes usually cinploycd l or vat-dyeing dycstull's, the new dyestull givcson nlunordanted cotton rod tints of a. great intensity and an excellent l'nstness to wzisl iii 1g. ll in the -hiregi)iiieg example smaller (unnlities of bromin-lor instance, only t iirtecn parts of broniiu -mm employed, the product of reaction, which contains less broniin, has analogous properties.

Exzuuple ll: Ina. suspension of four parts, byu-cight, of the condensation produetof one molecule alphaoxythionaphthene (thioindoxyl) or salicylthioacetic acid and one inolecule iszitinin about forty arts of glacial acetic acid a current of chlorin is led until an increased weight of four parts may be ascertained. The crystalline brownish-red rodnet of reaction is then separated by l1ltration, washed with alcohol, and dried. The dycstull' thus obtained dissolves in concentrated sulfuric acid with a browi'i coloration. ()n adding water to this sulfuric solution brilliant red flocks separate. I uming-sulfuric acid. gives a Violet-rod solution with forms. tion of a sulfonic acid of the dyestufl'. On addition of Water to this latter solution a. clear brown-rcd solution is 0l)tained,'which dyes wool in lively red shades. The dyestufl is dillicultly soluble in hot alcohol and hot bcn zene with a rose coloration; but it is easily soluble in hot nitrobenzcne With an intense red coloration. When applied on cotton by dyeing or printing, by means of the known processes, the dyestull yields red tints which are yellower, purer, and also faster to Washing than the tints obtained by the not chlorinated product. In an analogous man ner may be obtained the halogenated derivatives of the condensation product of salicylthioacetic acid or alplmoxythionaphthene (thioindoxyl) with methylisetin, isatinchlorid, or another isetin compound.

What I claim is 1. The process for the manufacture of red vet-dyeing dyestuffs bytreet'ing with a halogen, in presence of an indifferent diluent, the products resulting from the condensation of one molecule of elpheoxythionaphthene (thi oindoxyl) with one molecule of an isatin compound.

2, As new products, the halogenated red vet-dyeing dyestufls derived from the hereinsFecificd condensation products ofalphaoxyt'llOIlflPhtllt-fllfi (thioindoxyl) with isatin brown-black coloration and solublein fuming sulfuric h-cid with red-violet eoloration becoming clear brown-red OhitddltlOIl of Water. IIIWIUIQSS whereof I have hereunto slgned my name, this 19th day of December, 1906, in v the presence of two subscribing Witnesses. GADIENT ENGI;

Witnesses:

Geo. GiFFom), AMAND RITTER. 

